64638-13-7

Upstream product

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 104-15-4 toluene-4-sulfonic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 108441-50-5 5-methyl-3'-azido-2',3'-dideoxyisocytidine 
• 106060-85-9 2,5'-anhydro-3'-azido-3',5'-dideoxythymidine 

Relevant academic research and scientific papers

Sugar-thioacetamide backbone in oligodeoxyribonucleosides for specific recognition of nucleic acids

The amide linkage being shorter than the natural phosphate linkage, an additional atom is introduced into oligodeoxyribonucleosides (ODNs) with sugar-thioacetamide backbone that show very good RNA recognition properties. The Royal Society of Chemistry 200

Synthesis of activated 3′-amino-3′-deoxy-2-thio-thymidine, a superior substrate for the nonenzymatic copying of nucleic acid templates

We present a scalable synthesis of 3′-amino-3′-deoxy-2-thio-thymidine-5′-phosphoro-2-methylimidazolide, an activated monomer that can copy adenosine residues in nucleic acid templates rapidly without a polymerase. The sulfur atom substitution enhances the

Antibacterial AZT derivative regulates metastasis of breast cancer cells

Antimicrobial peptides (AMP) with anticancer activity have drawn remarkable attention in modern treatments. However, long peptide length and protease instability are the most addressing factors, which hampers their further development as therapeutic agents. In view of this, herein, we designed and synthesized a series of AZT-based cationic small molecule incorporating a variety of hydrophobic groups and cationic charges, including amine and guanidine groups to mimic the amphipathic structure of AMPs. These compounds were evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria. Through an extensive structure activity relationship study (SAR), we identified ADG-2e as the most potent antibacterial agent, which exhibited remarkable potency against drug resistant bacterial strains such as MRSA and MDRPA. Further, ADG-2e was examined for their anti-metastatic ability by investigating the cancer cell migration and invasiveness through scratch wound-healing assay and transwell invasive assay, respectively. In addition, time-lapse cell tracking analysis also performed for analyzing the cell movement pattern. Treatment of ADG-2e against metastatic breast cancer cells (MDA-MB-231) suppressed tumor cell migration by multi-directional lamellipodium formation, indicating their anti-metastatic potential. Thus, our cationic AZT based small molecules may evolve as an appealing class of antibacterial agents with anti-metastasis potential.

Amphipathic small molecule azt compound displays potent inhibitory effects in cancer cell proliferation

Cancer has been identified as a leading cause of death worldwide, and the increasing number of cancer cases threatens to shorten the average life expectancy of people. Recently, we reported a 3-azido-3-deoxythymidine (AZT)-based amphipathic small molecule, ADG-2e that revealed a notable potency against tumor metastasis. To evaluate the anticancer potential of ADG-2e, we assessed its anticancer potency in vitro and in vivo. Anticancer screening of ADG-2e against cervical cancer cells, HeLa CCL2, and BT549 mammary gland ductal carcinoma showed significant inhibition of cancer cell proliferation. Furthermore, mechanistic investigations revealed that cancer cell death presumably proceeded through an oncosis mechanistic pathway because ADG-2e treated cells showed severe damage on the plasma membrane, a loss of membrane integrity, and leakage of α-tubulin and β-actin. Finally, evaluation of the antitumorigenic potential of ADG-2e in mouse xenograft models revealed that this compound potentially inhibits cancer cell proliferation. Collectively, these findings suggest that ADG-2e can evolve as an anticancer agent, which may represent a model for nucleoside-based small molecule anticancer drug discovery.

Synthesis and antiviral evaluation of 3'-substituted thymidine analogues derived from 3'-amino-3'-deoxythymidine

To assess the structure-activity relationship for antiviral activity, a series of 3'-deoxy-3'-N-functionalized thymidine analogues were synthesized. Several of these thymidine analogues show moderate in vitro activity against HIV-1 and HIV-2.

Synthesis and antiviral evaluation of 3′-substituted thymidine analogues derived from 3′-amino-3′-deoxythymidine

Based on the structure-activity relationship for antiviral activity, a series of 3′-deoxy-3′-N-functionalized thymidine analogues derived from 3′-amino-3′-deoxythymidine was synthesized. These compounds were evaluated for their antiviral activity. Three of the prepared molecules namely 3′-(1,2,4-triazol-1-yl)carbimidoylamino-3′-deoxythymidine 6, 3′-(3-amino-1-methyl-1,2,4-triazol-5-yl)amino-3′-deoxythymidine 8b and 3′-N-cyano-O-phenylisourea-3′-deoxythymidine 7 show moderate but selective in vitro activity against HIV-1 and HIV-2. These data demonstrate that some steric bulk in the 3′-position is compatible with anti-HIV activity. Copyright

Lipidic Peptides, IX Synthesis and Structural Elucidation of Lipophilic Azidothymidine Conjugates

Azidothymidine (AZT) esters of lipidic amino acid and oligomers, together with AZT-5'-lipidic sulphide were synthesised.The AZT conjugates with ester linkages (3a-e) were prepared by coupling the lipidic amino acids and their oligomers to the 5'-hydroxyl

Synthesis and Antiviral Activity of Several 2,5'-Anhydro Analogues of 3'-Azido-3'-deoxythymidine, 3'-Azido-2',3'-dideoxyuridine, 3'-Azido-2',3'-dideoxy-5-halouridines, and 3-Deoxythymidine against Human Immunodeficiency Virus and Rauscher-Murine Leukemia

Several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AZU), 3'-azido-2',3'-dideoxy-5-bromouridine, 3'-azido-2',3'-dideoxy-5-iodouridine, and 3'-deoxythymidine and the 3'-azido derivative of 5-methyl-2'-deoxyiso

A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.

A novel synthetic procedure has been developed for the large-scale synthesis of 5-chloro-, 5-bromo-, and 5-iodo-5'-amino-2',5'-dideoxyuridine (4c-e) as well as of two new analogues, 5-iodo-5'-amino-2',5'-dideoxycytidine and 5-fluoro-5'-amino-2',5'-dideoxyuridine (4a and 4b), in good yield. The starting materials, 5-halo-2'-deoxyuridine and 5-halo-2'-deoxycytidine, are readily available and the method is straightforward. This report describes the synthesis and the biologial activities of these compounds.